2 Beds ⋅ 2 Baths ⋅ 100588702 MLS ⋅ Hyland Hills BLDG.

LOCATION AND CONVENIENCE! SHORT TERM RENTALS PERMITTED A mere 8 minutes from the dining, shopping and fun in quaint downtown Southern Pines! 30 minutes from Fort Bragg! Calling all golfers, investors and first time home buyers! This second story condo located adjacent to the newly restored Hyland Golf Club offers the perfect 'lock and leave' lifestyle. The current owner has invested in the 'BIG' concerns - HVAC replaced in 2022 and hot water heater replaced in 2019 - in addition to new stainless steel appliances - convection oven, dishwasher and refrigerator. The washer and dryer are included for the next owners. Top of the line Ecobee smart thermostat for energy savings. The living room offers views of the golf course, and the enclosed balcony offers blinds, plexiglass windows for cooler months, and of course screens! The layout is ahead of it's time, with an open concept kitchen and living area, and a 'split' floor plan for the two bedrooms. Enjoy the true laundry room (not just a closet) as well as storage underneath the stairs leading to the unit, and a dropstair attic with storage for decorations and other light objects. Zoned for McDeeds Creek Elementary, Crains Creek Middle School and Pinecrest High. STARS Charter School (K-8) is just up the street. The driving range is a stone's throw from your door, and the Tom Jackson designed Hyland Golf Course itself offers daily play, Champion mini-dwarf Bermuda greens, sparkling water, tall pines, and is known as the ''players'' course. The nearby clubhouse offers a snack bar and pro shop. The property will be sold 'as-is', with seller making no repairs. Don't miss out on this incredible opportunity!

504 Fairway Ct, Southern Pines

Courtesy of Keller Williams Pinehurst

$1,145,000

4 Beds ⋅ 4 Baths ⋅ LP763553 MLS

The Maplewood Cottage (2,932 sq ft) is complemented by a fully furnished detached guest house (479 sq ft), creating a property that combines flexible living space, privacy, and the character of Weymouth Heights Historic District within one of Southern Pines' most established residential settings. Thoughtfully updated while preserving the scale and feel of the surrounding neighborhood, the property offers five bedrooms, multiple gathering spaces, and strong connections between indoor and outdoor living. Just off the front entry, a more intimate sitting room creates a welcoming introduction to the home. Beyond the double doors, the main living spaces open into the great room and adjoining Carolina room, where vaulted ceilings, expansive windows, and views of the surrounding landscape create a natural focal point. French doors, exposed brick accents, and strong sight lines throughout the rear living areas reinforce the connection between the interior spaces and the mature pines beyond. The kitchen, dining, and living areas are comfortably integrated to create a functional and inviting central living space. The renovated kitchen balances function and design with stone countertops, ceramic tile backsplash, Bertazzoni gas range, and a large central island that anchors the space naturally. Adjacent to the kitchen, the butler's pantry includes a wet bar along with additional storage and serving space. The primary suite features custom armoire-style storage, fireplace feature wall, and a spacious bath with dual vanity and large walk-in shower. Expansive windows throughout the home bring in soft natural light and reinforce the connection to the surrounding property. Outdoor spaces feel private and well established, with brick patios, garden paths, mature landscaping, and a large fenced backyard that includes a separate white picket enclosed area accented with copper-capped detailing. One patio connects directly to the primary suite and hot tub area, while another extends from the rear living spaces beneath the canopy of mature trees. Above the detached two-car garage, the fully furnished, turn-key guest house extends the functionality of the property, offering a comfortable and well-designed space for visitors or longer-term stays. Complete with a full bath, kitchenette, and open living area, it provides flexibility while maintaining privacy from the main residence. A short distance from downtown Southern Pines and the trails of Weymouth Woods, the property is well positioned for both daily convenience and outdoor recreation. Residents enjoy easy access to Broad Street's locally owned restaurants, shops, and historic downtown character, along with miles of nearby walking trails through protected longleaf pine forest characteristic of the Sandhills region. This 1.68 acre property offers a distinctive combination of privacy, updated living space, guest accommodations, and proximity to both downtown Southern Pines and Weymouth Woods within one of the area's most established neighborhoods.

305 Maples Rd, Southern Pines

Seller Representative EVERYTHING PINES PARTNERS LLC

$1,145,000

4 Beds ⋅ 4 Baths ⋅ 763553 MLS

The Maplewood Cottage (2,932 sq ft) is complemented by a fully furnished detached guest house (479 sq ft), creating a property that combines flexible living space, privacy, and the character of Weymouth Heights Historic District within one of Southern Pines' most established residential settings. Thoughtfully updated while preserving the scale and feel of the surrounding neighborhood, the property offers five bedrooms, multiple gathering spaces, and strong connections between indoor and outdoor living. Just off the front entry, a more intimate sitting room creates a welcoming introduction to the home. Beyond the double doors, the main living spaces open into the great room and adjoining Carolina room, where vaulted ceilings, expansive windows, and views of the surrounding landscape create a natural focal point. French doors, exposed brick accents, and strong sight lines throughout the rear living areas reinforce the connection between the interior spaces and the mature pines beyond. The kitchen, dining, and living areas are comfortably integrated to create a functional and inviting central living space. The renovated kitchen balances function and design with stone countertops, ceramic tile backsplash, Bertazzoni gas range, and a large central island that anchors the space naturally. Adjacent to the kitchen, the butler's pantry includes a wet bar along with additional storage and serving space. The primary suite features custom armoire-style storage, fireplace feature wall, and a spacious bath with dual vanity and large walk-in shower. Expansive windows throughout the home bring in soft natural light and reinforce the connection to the surrounding property. Outdoor spaces feel private and well established, with brick patios, garden paths, mature landscaping, and a large fenced backyard that includes a separate white picket enclosed area accented with copper-capped detailing. One patio connects directly to the primary suite and hot tub area, while another extends from the rear living spaces beneath the canopy of mature trees. Above the detached two-car garage, the fully furnished, turn-key guest house extends the functionality of the property, offering a comfortable and well-designed space for visitors or longer-term stays. Complete with a full bath, kitchenette, and open living area, it provides flexibility while maintaining privacy from the main residence. A short distance from downtown Southern Pines and the trails of Weymouth Woods, the property is well positioned for both daily convenience and outdoor recreation. Residents enjoy easy access to Broad Street's locally owned restaurants, shops, and historic downtown character, along with miles of nearby walking trails through protected longleaf pine forest characteristic of the Sandhills region. This 1.68 acre property offers a distinctive combination of privacy, updated living space, guest accommodations, and proximity to both downtown Southern Pines and Weymouth Woods within one of the area's most established neighborhoods.

305 Maples Road, Southern Pines

Courtesy of EVERYTHING PINES PARTNERS LLC

$1,100,000

100421261 MLS

By Appointment only.......Stunning 11.45 fenced acreage ready for you to build out your slice of Horse Heaven. Property includes a 250'x130' arena and a 60' wide covered round pen with fiber GGT-footing, suitable for all types of equestrian uses. Deeded easement along property line for Walthour- Moss Foundation access. Waterlines and hydrants throughout the property are currently on a well shared with 2753 Youngs Rd (MLS 100421306). A new well to be installed by Buyer after closing at Buyers cost. A short term shared well agreement will be drawn up during Due Diligence.

Tbd Tbd Goodwill Rd, Southern Pines

Courtesy of Better Homes and GardensReal Estate Lifestyle Property Partners/SP

Buyer Representative Better Homes and GardensReal Estate Lifestyle Property Partners/SP

$515,000

4 Beds ⋅ 2 Baths ⋅ 100383263 MLS

HIGH PRODUCING SHORT TERM RENTAL. IN THE HEART OF DOWNTOWN SOUTHERN PINES - Enjoy evenings on the porch or the landscaped backyard. Just a few blocks from downtown Southern Pines. Whether it be for investment or permanent residence this quaint beauty is a fabulous opportunity to own in the highly desirable Downtown Southern Pines area. Hardwood floors and smooth ceilings.. Great outdoor workshop/multipurpose shed. Master BR has a relaxing reading area perfect for a good book.. 4th BR or bonus room. Move in Ready, All furniture and furnishings are fully negotiable.

145 Duffers Ln, Southern Pines

Courtesy of Premier Real Estate of the Sandhills LLC

Buyer Representative Carolina Property Sales

$499,000

3 Beds ⋅ 2 Baths ⋅ LP741109 MLS

Have you ever seen the show ''Gilmore Girls'' Showcasing the town Stars Hollow? If Southern Pines was a made for television town, I liken it to Stars Hollow . The lifestyle of small town living is romantically captured here. Downtown Southern Pines is friendly, hip, and charming. Don't miss out on this INCOME EARNING RANCH HOME for Sale. Welcome to Southern Pines. This lock & leave home is centrally located in the thriving downtown area. Streets lined with side walks connecting downtown make for easy access to amenities like a wide variety of parks, gyms, boutique shopping, restaurants and the nightlife. I've heard ..... living downtown enhances your quality of life? Located in the historic district, being utilized as a short term rental home. The word on the street is '' THIS HOME IS A GUEST FAVORITE'' 2 minutes walk from the park 3 minutes walk from the main strip Broad STREET

280 S Ashe St, Southern Pines

Seller Representative LOVE PINES REALTY

Buyer Representative

$384,000

2 Beds ⋅ 2 Baths ⋅ 100556273 MLS

Price Improvement of $20k! Welcome to 311 N Saylor! A property that represents the quaint cottage style so often seen throughout Southern Pines. This home was the primary residence of the current owners who then turned it into a profitable short-term rental. Proof of profitability available upon request. Whether you are looking to invest in a rental property or make this your primary residence, 311 N Saylor has the qualities to fit your needs. Being walkable to downtown Southern Pines, you or your guests will find some of Moore County's best restaurants and shops. On the property, you will find a well constructed, fully fenced in back yard which includes a detached single car garage - perfect for extra parking, storage, or other entertainment space. Additionally, there is a private patio looking over an expansive back yard not often seen in downtown properties. Inside, is a very modern layout with updated features and appliances. The floor plan is efficient where the living room, dinning, and kitchen flow right into own another and the bedrooms have just enough privacy. At the back of the home, you'll pass through a kitchen with a beautiful island to find that there is a dedicated laundry space just before you reach the access to the private patio. All furniture on the property will convey at closing and there is also an assumable VA loan available for qualified buyers.

311 N Saylor St, Southern Pines

Courtesy of Village of Pinehurst Rentals, LLC

Buyer Representative Keller Williams Pinehurst

$342,000

3 Beds ⋅ 3 Baths ⋅ 100555148 MLS

This beautiful townhome offers the perfect blend of comfort, style, and convenience. Located in the heart of Southern Pines, you're just minutes from local dining, shopping, parks, coffee shops, and everything that makes this area so desirable. Inside, you'll find warm hardwood flooring, a spacious and functional layout, and great natural light throughout the main living areas. The living room flows seamlessly into the dining space and kitchen, making everyday living and entertaining feel effortless. The kitchen features ample cabinet space, stainless appliances, and a layout designed for both function and style. The home offers generously sized bedrooms, including a comfortable primary suite. The floor plan is thoughtfully designed with a full bathroom on the main level for guests and everyday convenience, plus a private primary bathroom and an additional full bathroom upstairs. Additional features include dedicated laundry space and storage throughout. The property has been utilized as a short-term rental and presents flexibility for a variety of ownership goals, whether as a primary residence, second home, or investment opportunity. Seller is offering the furnishings currently in the home as a separate purchase, providing a potential turnkey opportunity for the next owner. Whether you're looking for a primary residence or investment opportunity in one of Moore County's most sought-after locations, this one checks the boxes.

255 E Delaware Ave Unit Unit F, Southern Pines

Courtesy of Keller Williams Pinehurst

Buyer Representative The Gentry Team

$545,000

3 Beds ⋅ 3 Baths ⋅ 100552035 MLS

This adorable downtown Southern Pines cottage is the kind of place buyers fall for fast. Currently operating as a successful short-term rental, it offers the flexibility to purchase as an established STR or make it your own primary residence. Inside, you'll find durable LVP flooring, granite countertops, and a layout that's both cozy and functional. Outside, the covered porch invites slow mornings with coffee, while the fire pit sets the scene for relaxed evenings under the stars. Location is everything, and this one absolutely delivers—just a short walk to Southern Pines' favorite shops, pubs, parks, and restaurants. Guests (or future you) can park the car and enjoy the best of downtown living on foot. Whether you're looking for a turnkey investment or a charming home with serious character, this cottage checks all the boxes: style, walkability, and income potential wrapped into one irresistible package.

430 N May St, Southern Pines

Courtesy of Realty World Properties of the Pines

Buyer Representative Keller Williams Pinehurst

$225,000

2 Beds ⋅ 2 Baths ⋅ 100549273 MLS ⋅ Hyland Hills BLDG.

Nestled beneath a canopy of mature longleaf pines, this charming 2-bedroom, 2-bath ground-level condo offers a rare blend of privacy and golf front living. Enjoy the view of the 8th fairway of Hyland Golf Course from the peaceful screened porch or off the private patio. Inside, the layout is comfortable and functional. Kitchen features granite countertops and stainless steel appliances. Ample storage can be found through the separate laundry room and a split bedroom floor plan. Located just minutes from everything Southern Pines has to offers golf, dining, shopping, and downtown amenities, this condo combines convenience with serenity. Whether you're seeking a personal escape, a short-term rental opportunity, or a smart investment, this property delivers versatility, location, and timeless Southern charm.

805 Dover St, Southern Pines

Courtesy of Berkshire Hathaway HS Pinehurst Realty Group/PH

Buyer Representative Carolina Property Sales

$525,000

3 Beds ⋅ 4 Baths ⋅ 100354707 MLS

You won't believe the Space & Storage in this Middleton Place Townhome! Single Level with Finished Basement plus additional In-Law Suite off Garage with 597 additional square feet.. Total Heated Sq Feet is 4666! Main Level has two Suites w/Full Baths. Lower Level has Bed/Bath plus many flex Rooms with Endless Possibilities. The Laundry, 4th Bed/Bath plus living/office space is accessed through the Garage. An Elevator is located in the Family room and can disappear with the push of a button to lower level. Notice the elevator movement in photos. Two Large Bricked Courtyards on each level are home owner Responsibility. Natural Gas for Fireplace and Gas Cook top. Roof Approx. Replaced in 2009/ HVAC Units 2018 & 2023 HOA dues are $375.00 monthly. Long Term Rentals Permitted/ Short Term are Not. All Landscaping is included, Road Maint, as well as Cable. Enjoy the Versatility this Amazing Home offers. Back Door to Deck Just Replaced.

32 Ashley Ct, Southern Pines

Courtesy of Berkshire Hathaway HS Pinehurst Realty Group/PH

Buyer Representative Berkshire Hathaway HS SP/Pinehurst Realty Group/SP

$410,000

5 Beds ⋅ 3 Baths ⋅ 100490441 MLS

Discover this exceptional investment in downtown, perfect for either rental income or owner-occupied living as upstairs was left vacant. This property features two distinct units: The downstairs unit offers 3 bedrooms and 2 bathrooms, currently leased as a long-term rental. The upstairs unit comprises 2 bedrooms and 1 bathroom, fully furnished and ideal for short-term or mid-term rentals. Enjoy the flexibility and convenience of its location along with its great character. New HVAC unit to be installed prior to closing in Downstairs unit to decrease maintenance and increase Net operating income.

465 W New Hampshire Ave, Southern Pines

Courtesy of eXp Realty

Buyer Representative Keller Williams Pinehurst

$610,000

3 Beds ⋅ 3 Baths ⋅ 100469578 MLS

$70,000 Price Improvement!!! Discover your perfect retreat just minutes from Downtown Southern Pines! This charming 1951-era offers a unique living arrangement. Main residence offers 2BR/2BA surrounded by 1 acre of lush privacy, featuring original trees and plantings surrounding this charming home of days gone by. Enjoy single-level living while appreciating the character of yesteryear. The attached 1BR/1BA apartment was added in the 1970's and is currently leased offering endless possibilities for short-term rentals, an in-law suite, family and guests...so many options. Apartment includes a private entrance, complete with living room, kitchen, bedroom and bath. Additional parking space works beautifully for guest and owner's privacy. Original cottage, Sold ''As Is'' with the property. Imagine all the possibilities with this gem location and unique opportunities. Embrace the tranquility of the Weymouth Heights location where you can stroll, bike and jog within a vibrant Downtown community—all nestled among the Longleaf Pines. A rare find in the heart of Southern Pines. Make your appointment to view this charming property today!

230 Pinegrove Rd, Southern Pines

Courtesy of Sandhill Realty/Aberdeen

Buyer Representative Keller Williams Pinehurst

$305,000

3 Beds ⋅ 1 Baths ⋅ 100405833 MLS

Escape to your enchanting countryside retreat nestled on nearly 2 acres of pure serenity! This charming 3-bedroom, 1-bathroom cottage with a fenced-in yard, offers a haven for those who cherish the tranquility of rural living without sacrificing modern convenience. From the moment you arrive, this picturesque cottage envelops you in timeless charm and warmth. Its unique character and fantastic location make it a magnet for those seeking a relaxing getaway, also presenting an excellent opportunity for short-term rentals or Airbnb investment. The cottage itself is a testament to rustic elegance. Featuring three cozy bedrooms and spacious bathroom, it provides a comfortable and inviting space to call home. The living areas exude a welcoming atmosphere, with natural light pouring in through quaint windows, showcasing the beautiful landscaped surroundings. What truly sets this property apart is its location. Tucked away in the heart of the countryside, you'll find peace and tranquility, far removed from the noise and stress of city life. Yet, you're never too far from essential amenities, ensuring that daily life remains convenient and stress-free. But that's not all! The property also includes a spacious outbuilding, offering over 1,000 square feet of versatile space. This workshop is a dream come true for hobbyists, DIY enthusiasts, or artists seeking a private studio. While it may require some TLC, Imagine the possibilities—breathe new life into this workshop, create your masterpiece, or turn it into an income-generating space. The choice is yours. Don't miss this opportunity to own a piece of countryside paradise! Welcome home!

166 N Connecticut Ave, Southern Pines

Courtesy of Realty Partners, LLC

Buyer Representative Everything Pines Partners LLC

$499,000

3 Beds ⋅ 2 Baths ⋅ 100497169 MLS

Cottage in DOWNTOWN Southern Pines! Have you ever seen the show ''Gilmore Girls'' Showcasing the town Stars Hollow? If Southern Pines was a made for television town, I liken it to Stars Hollow . The lifestyle of small town living is romantically captured here. Downtown Southern Pines is friendly, hip, and charming. Don't miss out on this INCOME EARNING RANCH HOME for Sale. Welcome to Southern Pines. This lock & leave home is centrally located in the thriving downtown area. Streets lined with side walks connecting downtown make for easy access to amenities like a wide variety of parks, gyms, boutique shopping, restaurants and the nightlife. I've heard ..... living downtown enhances your quality of life? Located in the historic district, being utilized as a short term rental home. The word on the street is '' THIS HOME IS A GUEST FAVORITE'' 2 minutes walk from the park 3 minutes walk from the main strip Broad STREET

280 S Ashe St, Southern Pines

Courtesy of Love Pines Realty

Buyer Representative Pineland Property Group LLC

$485,000

3 Beds ⋅ 3 Baths ⋅ 100450289 MLS

Welcome to 75 Station Avenue, a charming Townhome located within the desirable neighborhood of Walker Station. This property comes with a Transferrable Charter Membership to Pinehurst Country Club! Upon entering, you are greeted by a sunny foyer & beautiful heart pine floors. The main living area is bright & airy with high ceilings, neutral paint, recessed lighting, a gas fireplace & plenty of windows to allow for natural light. Natural gas runs to this property & services the fireplace, gas range & Tankless water heater. The kitchen features white shaker cabinets, gorgeous granite countertops, stainless appliances with Gas Range. Both of the full bathrooms have matching white shaker cabinetry, w/ granite countertops bringing a cohesive feel to the home. The primary suite is on the main level with walk in closet, tiled shower & double Vanity. The laundry room is spacious with a folding counter & drop zone. The second floor offers two additional bedrooms & full bath. Each bedroom is well designed, generously sized with large closets for all your storage needs. The fully fenced in backyard with deck and patio are perfect for entertaining. Two car attached garage provides plenty of storage space with additional unfinished space above for another 200 sq. ft. of potential living space. Walker Station is conveniently located just minutes from both Southern Pines and the Village of Pinehurst. The Southern Pines Greenway Trail System is adjacent to this neighborhood which also leads to the Reservoir Park. A community pool, pool house, gazebo, & sidewalks round out this perfect place to call home. All Appliances, Kitchen Fridge Convey. HOA $265.00 a Month. Rentals are permitted with min. 1 year commitment. No short term renting permitted. Seller needs a 2 week lease back post closing.

75 Station Ave, Southern Pines

Courtesy of Berkshire Hathaway HS Pinehurst Realty Group/PH

Buyer Representative Keller Williams Pinehurst

$290,000

2 Beds ⋅ 2 Baths ⋅ 100520340 MLS ⋅ Longleaf CC BLDG.

Discover the perfect blend of investment potential and personal retreat at Longleaf Country Club—home of U.S. Kids Golf! This ground-floor 2 bedroom, 2 bath unit sits on the golf course and offers excellent short-term rental potential or a relaxing getaway of your own. Enjoy a gas log fireplace, well-appointed kitchen and dining area, a covered front porch with seating area, and a spacious covered back patio overlooking the fairway. Whether you're looking for income, relaxation, or both—this one checks all the boxes!

48 N Knoll Rd, Southern Pines

Courtesy of eXp Realty

Buyer Representative Coldwell Banker Advantage-Southern Pines

$825,000

4 Beds ⋅ 3 Baths ⋅ 100422090 MLS

Ridge View Cottage is a stunning home in the heart of downtown Southern Pines! This four bed room three bath offers three bedrooms on the main floor and a fourth that is in the guest suite and can be accessed from the main house or a separate entrance...perfect for a US Open rental, short term or long term rental (the current owner has been offered $2700 for a long term rental). The location and condition of this beautiful home doesn't get better than this! This home sits within one block to multiple attractions including Downtown Southern Pines, The Weymouth Center and State Park with miles of trails, 305 Trackside Venue and all the shops and restaurants of Southern Pines, the historic Campbell House Park that includes a golf hole, playground, soccer field, Train House, and baseball field...all right outside your backyard! The main house has been completely updated in the last year including painting inside and out, popcorn ceilings removed, new gutters, new shiplap fireplace, professionally updated landscaping, whole house exterior sprinkler system and so much more! See Feature Sheet with all the upgrades! The main floor offers three bedrooms, two baths and an oversized Great Room with natural gas fireplace (the HVAC, range and dryer are natural gas, too!), large kitchen with beautiful granite countertops, an island and a built in bench. The dining area fits a large farm house table but could also be used as a den. This flows out to the covered patio and fire pit area. Perfect for entertaining! The backyard is fully fenced and also offers a water feature. The fully sustainable guest apartment called ''The Nest'' offers a full kitchen, private laundry, storage, a spacious full bathroom, walk in closet, sleeping area and mini guest room or office space! Everything in the guest apartment is new. It truly is a special space! Come home to Ridge View Cottage and The Nest now before it is too late!

225 N Ridge St, Southern Pines

Courtesy of McDevitt Town & Country Properties

Buyer Representative Realty World Properties of the Pines

$499,000

3 Beds ⋅ 2 Baths ⋅ 741109 MLS

Have you ever seen the show ''Gilmore Girls'' Showcasing the town Stars Hollow? If Southern Pines was a made for television town, I liken it to Stars Hollow . The lifestyle of small town living is romantically captured here. Downtown Southern Pines is friendly, hip, and charming. Don't miss out on this INCOME EARNING RANCH HOME for Sale. Welcome to Southern Pines. This lock & leave home is centrally located in the thriving downtown area. Streets lined with side walks connecting downtown make for easy access to amenities like a wide variety of parks, gyms, boutique shopping, restaurants and the nightlife. I've heard ..... living downtown enhances your quality of life? Located in the historic district, being utilized as a short term rental home. The word on the street is '' THIS HOME IS A GUEST FAVORITE'' 2 minutes walk from the park 3 minutes walk from the main strip Broad STREET

280 S Ashe Street, Southern Pines

Courtesy of LOVE PINES REALTY

Buyer Representative Non Member Office

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